Methallyl chloride

Methallyl chloride
Names
Preferred IUPAC name
3-Chloro-2-methylprop-1-ene
Other names
Isobutenyl chloride
Identifiers
CAS Number
  • 563-47-3
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:82419
ChEMBL
  • ChEMBL157368
ChemSpider
  • 21106501
ECHA InfoCard 100.008.411 Edit this at Wikidata
EC Number
  • 209-251-2
KEGG
  • C19363
PubChem CID
  • 11241
RTECS number
  • UC8050000
UNII
  • 7A9X1C3I3O
UN number 2554
CompTox Dashboard (EPA)
  • DTXSID1020279 Edit this at Wikidata
InChI
  • InChI=1S/C4H7Cl/c1-4(2)3-5/h1,3H2,2H3
    Key: OHXAOPZTJOUYKM-UHFFFAOYSA-N
  • CC(=C)CCl
Properties
Chemical formula
 C4H7Cl
Molar mass 90.55 g·mol−1
Appearance Colorless liquid
Density 0.9210 g/cm3 (15 °C)
Boiling point 71–72 °C (160–162 °F; 344–345 K)
Hazards
GHS labelling:
Pictograms
 GHS02: FlammableGHS05: CorrosiveGHS06: ToxicGHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Danger
H225, H302, H314, H317, H331, H335, H336, H351, H361, H372, H373, H411
P201, P202, P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P272, P273, P280, P281, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P308+P313, P310, P311, P312, P314, P321, P330, P333+P313, P363, P370+P378, P391, P403+P233, P403+P235, P405, P501
Flash point −12 °C (10 °F; 261 K)
Autoignition
temperature
 540 °C (1,004 °F; 813 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound

Methallyl chloride is the organic compound with the formula CH2=C(CH3)CH2Cl. It is a colorless liquid and a lacrymator. Its properties are similar to those of allyl chloride. It is a strong alkylating agent used to install isobutenyl groups.[1]

Reactivity

It is also a precursor to methallyl ligand. It is an isomer of crotyl chloride.

Methylenecyclopropane can be synthesised via an intramolecular cyclisation reaction from methallyl chloride by treatment with a strong base such as sodium amide.[2]

References

  1. ^ Krook, Mark A.; O'Doherty, George A.; Gao, Dong (2007). "Methallyl chloride". e-EROS Encyclopedia of Reagents for Organic Synthesis. pp. 1–6. doi:10.1002/9780470842898.rm061.pub2. ISBN 978-0471936237.
  2. ^ Salaun, J. R.; Champion, J.; Conia, J. M. (1977). "Cyclobutanone from Methylenecyclopropane via Oxaspiropentane". Organic Syntheses. 57: 36. doi:10.15227/orgsyn.057.0036.